Hydrochloric Acid → HCID 642500, compound

HRID 1437834Notes

Reaction equation

HRID 1437834 reaction equation
[Cl:1][C:2]1[C:3]([OH:12])=[CH:4][C:5]([OH:11])=[C:6]([C:9]=1[CH3:10])[CH:7]=[O:8].[CH:13](=[O:25])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24].O.O.[Cl-].[Ca+2].[Cl-].CO.[OH-].[K+].Cl>>[Cl:1][C:2]1[C:3]([OH:12])=[CH:4][C:5]([OH:11])=[C:6]([C:9]=1[CH3:10])[CH:7]=[O:8].[Cl:1][C:2]1[C:3]([OH:12])=[C:4]([CH:13]([OH:25])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[C:5]([OH:11])=[C:6]([C:9]=1[CH3:10])[CH:7]=[O:8]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 8194DodecanalHCID 642500HCID 642500, compoundHCID 6093260Calcium chloride, dihydrateHCID 23689386Potassium hydroxide methanol

Product 2

HCID 642500HCID 642500, compoundYield 61%HCID 23134889HCID 23134889, compoundYield 20%

Procedure

5-Chloro-2,4-dihydroxy-6-methylbenzaldehyde (112 mg, 0.60 mmol) described in M. M. Joullie et al., J. Org. Chem., 50, 3997 (1985), dodecanal (133 mg, 0.72 mmol) and calcium chloride dihydrate (58 mg, 0.40 mmol) were stirred in a 0.4 M potassium hydroxide methanol solution (2 ml) at 0° C. for 24 hours. The reaction mixture was made acidic with 1 M hydrochloric acid, extracted with ethyl acetate, and after post-treatment, the crude product was purified by silica gel thin-layer chromatography (chloroform:ethyl acetate=15:1) to obtain 5-chloro-2,4-dihydroxy-6-methylbenzaldehyde (68 mg, recovery 61%) and 5-chloro-2,4-dihydroxy-3-(1-hydroxydodecyl)-6-methylbenzaldehyde (45 mg, yield 20%).

Workup

  1. extractionextracted with ethyl acetate
  2. customafter post-treatment, the crude product was purified by silica gel thin-layer chromatography (chloroform:ethyl acetate=15:1)

Sources & evidence

ORD record
ord-38a243b350184aa791e696345296b9ba
Source dataset
uspto-grants-2009_11
Patent number
US07622598B2

Reaction notes

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